9 of the Cheapest Rolex Watches for Men

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Rolex has long been associated with luxury, quality, craftsmanship and (of course) the price tag that usually accompanies those things…

…so I’ll be the first to admit that an article rounding up the cheapest Rolex watches for men is more than a little oxymoronic.

A silver Rolex watch on an all black background

Long known as one of the most luxurious and expensive watch brands in the world, there’s certainly no such thing as a cheap Rolex.

(Unless you’ve accidentally bought a knock off, of course.)

But some models are, if not cheap, at least less expensive than others.

If you’re on a budget, the bad news is that the range of Rolexes available to you definitely isn’t as wide as it would be if you had bottomless pockets.

But the good news is that affordable Rolex watches do in fact exist, and it’s possible to buy one without refinancing your house or selling your car.

In this post I’ll round up some of the cheapest Rolex watches for men, and show you where and how to get your hands on an iconic, real and (relatively) affordable Rolex.

The Cheapest Rolex Watches for Men

(And, again, “cheap” is a relative term when it comes to Rolexes)

Affordable Option 1:

Buy an Entry-Level Rolex New

A silver Rolex watch with blue lighting on a man's wrist

It’s definitely possible to buy an affordable Rolex brand new.

But as soon as you combine the words “affordable” and “Rolex,” you’re going to be quite limited by the types of Rolexes that you can get.

Rolexes come in various series and collections, of which the Datejust collection is among the most affordable.

Each of the watches below falls into that category, which is why there are only slight variations between them.

But what this batch lacks in diversity it makes up for in affordability and value:

The most expensive watch below clocks in (clock pun very much intended) at less than $8,000, whereas on the high end Rolexes can easily go for 15, 20 or even 30 thousand dollars.

Rolex Oyster Perpetual 34 Purple Grape Dial

Price: $5,295
  • Series: Oyster Perpetual
  • Stainless Steel Bracelet
  • Automatic
  • Case Size: 34 mm

Adding a Rolex Oyster to your watch collection for less than $6,000 is an absolute steal.

(Maybe it’s because the purple watch face isn’t for everyone, but whatever the reason, this is a list price you won’t find very often.)

This watch has all the high-quality features you’d expect from the Oyster series, including the Rolex Calibre 3130 engine, a stainless steel case and a scratch-resistant sapphire crystal dial.

Learn More ➤


Rolex Oyster Perpetual 34 Olive Dial

Price: $5,495
  • Series: Oyster Perpetual
  • Stainless Steel Bracelet
  • Automatic
  • Case Size: 34 mm

Coming in at just $200 more than the purple-faced Oyster above, this version of the same watch has a (probably more crowd-pleasing) olive colored face.

While it may not stand out quite as much as its grape-colored counterpart, a lot of guys will probably view that as a good thing.

Other than the face color, the details here are largely the same as the one above:

It comes with the same Oyster case and stainless steel Oyster bracelet, along with all the other high-quality features that make a Rolex so sought after.

Learn More ➤


Rolex Oyster Perpetual 36 Black Dial

Price: $5,695
  • Series: Oyster Perpetual
  • Stainless Steel Bracelet
  • Automatic
  • Case Size: 36 mm

Moving up in both size and price, this 36 mm Oyster has a sleek and sophisticated black watch face.

To my eye it looks like the kind of timepiece James Bond would pair with his tux and martini, but still manages to come in under $6,000, making it a hell of a steal.

Learn More ➤


Rolex Air-King Silver Dial Stainless Steel

Price: $6,150
  • Series: Air King
  • Stainless Steel Bracelet
  • Automatic
  • Case Size: 34 mm

This 34 mm luxury watch is the most affordable Air King, the Rolex collection that “pays tribute to the pioneers of flight.”

With a silver toned watch face and use of Arabic numerals for the 3, 6 and 9 o’clock positions, it’s the kind fo classically timeless piece you can wear with just about anything—and pass down to your son to do the same.

Learn More ➤


Rolex Air-King Blue Arabic Dial

Price: $6,150
  • Series: Air King
  • Stainless Steel Bracelet
  • Automatic
  • Case Size: 34 mm

Another Airking, this one steps up the style with a blue watch face, and large Arabic numerals in orange and gray.

It’s both sportier and easier to read than some of the other options on this list, and at just a shade over $6,000 still quite affordable (as Rolexes go, of course).

Learn Mored ➤


Rolex Oyster Perpetual Date 34 Blue Dial

Price: $6,500
Rolex Oyster Perpetual Date 34 Blue Dial
  • Series: Oyster Perpetual
  • Stainless Steel Bracelet
  • Automatic
  • Case Size: 34 mm

Another entry from the Oyster Perptual Series, this one is an absolute stunner.

The Perpetual Date 34 has a smaller profile than most men’s watches, which only adds to the sophistication provided by its classic style and timeless design.

With an easy to read date window and a show-stopping blue watch face, in my opinion this is the best Rolex for the money, at least in terms of style.

Learn More ➤


Rolex Datejust 36 Automatic White Dial

Price: $7,195
Rolex Datejust 36 Automatic White Dial
  • Series: Datejust
  • Stainless Steel Bracelet
  • Automatic
  • Case Size: 36 mm

With a 36mm case instead of 34, this next entry from the Rolex Datejust series is slightly larger than the Oyster case above.

It also has a more classic white dial, and is further distinguished by its use of Roman numeral dial markers.

Learn More ➤


Rolex Datejust 36 Automatic White Dial

Price: $7,495
Rolex Datejust 36 Automatic White Dial
  • Series: Datejust
  • Stainless Steel Jubilee Bracelet
  • Automatic
  • Case Size: 36 mm

Another 36 mm entry from the Datejust series, this watch is similar to the one above.

But this one features a different band style:

Here, the bracelet is made from Rolex’s stainless steel jubilee material.

Learn More ➤


Rolex Datejust 36 Automatic Silver Dial

Price: $7,595
Rolex Datejust 36 Automatic Silver Dial
  • Series: Datejust
  • Stainless Steel Bracelet
  • Automatic
  • Case Size: 36 mm

This is an alternate version of the two 36 mm Datejust watches above.

This model features a silver face and luminescent silver-tone hands and dials, with automatic movement and a Rolex Calibre 3235 engine.

Learn More ➤


Affordable Option 2:

Buy a Pre-Owned Rolex

A vintage Rolex sitting on a red book

Another way to buy a cheap Rolex is to pick up one that was previously owned.

Buying a used Rolex is kind of like buying a used car:

There’s risk involved, but if you buy from a reputable dealer, it ultimately leads to much better value than if you bought a brand new model.

Buying used is probably your best bet if you’re looking for some of the really high-end collections, like the Roelx Submariner or Rolex Explorer.

The top-of-the-line collections cost a lot more because they tend to use even higher-end martials, including precious metals like white gold and yellow gold.

One of the best places to buy a pre-owned Rolex at lower prices than you’d normally pay is Jomashop.

If you haven’t heard of them, they’re a New York-based retailer that specializes in selling new and pre-owned watches and jewellery.

With a pretty wide selection of pre-owned Rolexes, they have lots of affordable options, including vintage models and collections that would be way out of reach if you weren’t buying used.

Plus they offer both a guarantee of authenticity on all products they sell, and their own warranty backing up your purchase.


FAQ

What is the cheapest Rolex?

If you’re buying new, the cheapest Rolex is the Oyster Perpetual Date 34, which features a stunning blue watch dial.

If you’re buying used, the cheapest model will vary, but opting for something hand wound could help keep the price down.

How much is the cheapest Rolex?

As mentioned above, the Oyster Perpetual Date 34 goes for $5,295 on Jomashop, which is a better price then you’d get through Rolex’s website.

But if you’re buying used, you can get one for much less; Jomashop offers multiple models for less than $5,000.


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More Style and Men’s Watch Advice and Recos from Irreverent Gent:

Banner image based on a (very cool) shot from Kimiya Oveisi via Unsplash (Thanks Kimiya!)

About

Irreverent Gent founder Dave Bowden is a men’s style specialist, an Amazon bestselling author, an unrepentant introvert, a long-suffering (but very patient) Toronto sports fan and the husband of a wonderful (and thankfully even more patient) wife.

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